TW201138799A - Novel 24-membered cyclooctadepsipeptides from fungal strains and their use as anthelmintics or endoparasiticides - Google Patents
Novel 24-membered cyclooctadepsipeptides from fungal strains and their use as anthelmintics or endoparasiticides Download PDFInfo
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- TW201138799A TW201138799A TW099143150A TW99143150A TW201138799A TW 201138799 A TW201138799 A TW 201138799A TW 099143150 A TW099143150 A TW 099143150A TW 99143150 A TW99143150 A TW 99143150A TW 201138799 A TW201138799 A TW 201138799A
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- 230000002538 fungal effect Effects 0.000 title claims abstract description 20
- 230000000507 anthelmentic effect Effects 0.000 title claims abstract description 5
- 239000000921 anthelmintic agent Substances 0.000 title claims abstract description 5
- 229940124339 anthelmintic agent Drugs 0.000 title abstract 2
- 241000082085 Verticillium <Phyllachorales> Species 0.000 claims abstract description 11
- 239000004377 Alitame Substances 0.000 claims abstract description 8
- 239000004159 Potassium persulphate Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 6
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims abstract description 3
- 241000223218 Fusarium Species 0.000 claims abstract description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 29
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 23
- 239000003610 charcoal Substances 0.000 claims description 10
- 241000233866 Fungi Species 0.000 claims description 8
- 230000000394 mitotic effect Effects 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000003096 antiparasitic agent Substances 0.000 claims description 4
- 241000233614 Phytophthora Species 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 3
- 241000589516 Pseudomonas Species 0.000 claims 1
- 229940079919 digestives enzyme preparation Drugs 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 6
- QVZZPLDJERFENQ-UHFFFAOYSA-N Bassianolide Natural products CC(C)CC1N(C)C(=O)C(C(C)C)OC(=O)C(CC(C)C)N(C)C(=O)C(C(C)C)OC(=O)C(CC(C)C)N(C)C(=O)C(C(C)C)OC(=O)C(CC(C)C)N(C)C(=O)C(C(C)C)OC1=O QVZZPLDJERFENQ-UHFFFAOYSA-N 0.000 abstract description 2
- 108010076663 bassianolide Proteins 0.000 abstract description 2
- QVZZPLDJERFENQ-NKTUOASPSA-N bassianolide Chemical compound CC(C)C[C@@H]1N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C(C)C)OC1=O QVZZPLDJERFENQ-NKTUOASPSA-N 0.000 abstract description 2
- 241000223679 Beauveria Species 0.000 abstract 1
- 241001183555 Coniolariella Species 0.000 abstract 1
- 241000221775 Hypocreales Species 0.000 abstract 1
- 241000221919 Phyllachorales Species 0.000 abstract 1
- 241001299709 Rosellinia Species 0.000 abstract 1
- 241001523964 Xylariaceae Species 0.000 abstract 1
- 230000002255 enzymatic effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 41
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 238000002101 electrospray ionisation tandem mass spectrometry Methods 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- 238000002474 experimental method Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- 239000001965 potato dextrose agar Substances 0.000 description 14
- 230000012010 growth Effects 0.000 description 12
- 102000004196 processed proteins & peptides Human genes 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 11
- 235000019253 formic acid Nutrition 0.000 description 11
- 229920001817 Agar Polymers 0.000 description 10
- 239000008272 agar Substances 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 108010002156 Depsipeptides Proteins 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 229930182558 Sterol Natural products 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 150000003432 sterols Chemical class 0.000 description 5
- 235000003702 sterols Nutrition 0.000 description 5
- 238000004885 tandem mass spectrometry Methods 0.000 description 5
- 241000218631 Coniferophyta Species 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 238000012216 screening Methods 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 108010029485 Protein Isoforms Proteins 0.000 description 3
- 102000001708 Protein Isoforms Human genes 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 239000006166 lysate Substances 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 108700028369 Alleles Proteins 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 241000223259 Trichoderma Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008223 sterile water Substances 0.000 description 2
- NGEWQZIDQIYUNV-SCSAIBSYSA-N (R)-2-hydroxy-3-methylbutyric acid Chemical compound CC(C)[C@@H](O)C(O)=O NGEWQZIDQIYUNV-SCSAIBSYSA-N 0.000 description 1
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 1
- 238000005084 2D-nuclear magnetic resonance Methods 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000751139 Beauveria bassiana Species 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 241000221955 Chaetomium Species 0.000 description 1
- 108010069514 Cyclic Peptides Proteins 0.000 description 1
- 102000001189 Cyclic Peptides Human genes 0.000 description 1
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 238000004252 FT/ICR mass spectrometry Methods 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241001660766 Labeo rohita Species 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 241001275898 Mylopharyngodon piceus Species 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 241001126260 Nippostrongylus Species 0.000 description 1
- 108010004210 PF 1022A Proteins 0.000 description 1
- YJNUXGPXJFAUQJ-LYWANRAQSA-N PF1022A Chemical compound C([C@@H]1C(=O)N(C)[C@H](C(O[C@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)O[C@H](CC=2C=CC=CC=2)C(=O)N(C)[C@@H](CC(C)C)C(=O)O[C@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)O1)=O)CC(C)C)C1=CC=CC=C1 YJNUXGPXJFAUQJ-LYWANRAQSA-N 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- 241000219492 Quercus Species 0.000 description 1
- 206010039710 Scleroderma Diseases 0.000 description 1
- 241000239226 Scorpiones Species 0.000 description 1
- 241000607768 Shigella Species 0.000 description 1
- 108010073771 Soybean Proteins Proteins 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- 241000243774 Trichinella Species 0.000 description 1
- 241000223238 Trichophyton Species 0.000 description 1
- 241000893966 Trichophyton verrucosum Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 241001523965 Xylaria Species 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 230000002141 anti-parasite Effects 0.000 description 1
- 229940125687 antiparasitic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 238000005100 correlation spectroscopy Methods 0.000 description 1
- JJWIOXUMXIOXQN-UHFFFAOYSA-N cyclohexadecane Chemical compound C1CCCCCCCCCCCCCCC1 JJWIOXUMXIOXQN-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001437 electrospray ionisation time-of-flight quadrupole detection Methods 0.000 description 1
- 244000079386 endoparasite Species 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
- 238000003929 heteronuclear multiple quantum coherence Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 238000000238 one-dimensional nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical compound O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 description 1
- 238000011218 seed culture Methods 0.000 description 1
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(I) nitrate Inorganic materials [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940001941 soy protein Drugs 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09178799 | 2009-12-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201138799A true TW201138799A (en) | 2011-11-16 |
Family
ID=43480707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW099143150A TW201138799A (en) | 2009-12-11 | 2010-12-10 | Novel 24-membered cyclooctadepsipeptides from fungal strains and their use as anthelmintics or endoparasiticides |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20120302496A1 (enExample) |
| EP (1) | EP2509967B1 (enExample) |
| JP (1) | JP5779787B2 (enExample) |
| AR (1) | AR079341A1 (enExample) |
| AU (1) | AU2010329998B2 (enExample) |
| TW (1) | TW201138799A (enExample) |
| UY (1) | UY33095A (enExample) |
| WO (1) | WO2011069995A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104540845B (zh) * | 2012-06-13 | 2018-01-26 | 明治制果药业株式会社 | 新的环缩酚酸肽衍生物以及含有它的有害生物防除剂 |
| WO2015093558A1 (ja) * | 2013-12-18 | 2015-06-25 | Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 | 環状デプシペプチド誘導体およびそれを含んでなる有害生物防除剤 |
| CN107835818B (zh) | 2015-05-20 | 2022-04-29 | 勃林格殷格翰动物保健美国公司 | 驱虫缩酚酸肽化合物 |
| KR20220003663A (ko) | 2015-12-28 | 2022-01-10 | 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 | 구충성 뎁시펩티드 화합물 |
| EP3541789A1 (en) | 2016-11-16 | 2019-09-25 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic depsipeptide compounds |
| CN106749569B (zh) * | 2017-03-03 | 2021-10-15 | 重庆乾泰生物医药有限公司 | 一种pf1022a的分离纯化方法 |
| CN108570016B (zh) * | 2017-03-10 | 2021-11-26 | 上海医药工业研究院 | 一种pf1022a分离纯化的方法 |
| CN106978353B (zh) * | 2017-03-10 | 2019-10-18 | 广东省微生物研究所 | 特氏炭角菌及其栽培方法 |
| CN113943350B (zh) * | 2021-11-02 | 2023-08-15 | 海南大学三亚南繁研究院 | 一种环肽化合物或其药学上可接受的盐及其制备方法和应用、药物及其应用 |
| CN114875093B (zh) * | 2022-05-20 | 2024-07-19 | 浙江海正药业股份有限公司 | 一种提高pf1022a发酵产量的方法 |
| WO2025149943A1 (en) * | 2024-01-09 | 2025-07-17 | Animol Discovery, Inc. | Antiparasitic cyclic depsipeptides |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO176766C (no) | 1989-02-07 | 1995-05-24 | Meiji Seika Kaisha | Fremgangsmåte for fremstilling av en forbindelse med anthelmintaktivitet |
| JP3207870B2 (ja) * | 1991-04-15 | 2001-09-10 | 明治製菓株式会社 | 環状デプシペプチドおよびその製造法 |
| JP2873894B2 (ja) * | 1992-10-19 | 1999-03-24 | 明治製菓株式会社 | 環状デプシペプチドおよびその製造法 |
| DE4317432A1 (de) * | 1993-05-26 | 1994-12-01 | Bayer Ag | Octacyclodepsipeptide mit endoparasitizider Wirkung |
| DE4341992A1 (de) | 1993-12-09 | 1995-06-14 | Bayer Ag | Endoparasitizide Mittel auf Basis von offenkettigen Tetradepsipeptiden |
| WO1998005655A1 (en) | 1996-08-07 | 1998-02-12 | Meiji Seika Kaisha, Ltd. | Process for producing cyclodepsipeptide compounds and novel cyclodepsipeptide |
| AU2009331930A1 (en) * | 2008-12-16 | 2011-06-30 | Bayer Animal Health Gmbh | Method for producing optically active, cyclic depsipeptides comprising lactic acid and phenyl lactic acid and having 24 ring atoms, using fungus strains of Rosellinia type, and further species of Xylariaceae |
| US9209940B2 (en) | 2009-03-16 | 2015-12-08 | Lg Electronics Inc. | Method of retransmission for supporting MIMO in synchronous HARQ |
-
2010
- 2010-12-07 EP EP10790400.5A patent/EP2509967B1/en not_active Not-in-force
- 2010-12-07 US US13/514,538 patent/US20120302496A1/en not_active Abandoned
- 2010-12-07 WO PCT/EP2010/069040 patent/WO2011069995A1/en not_active Ceased
- 2010-12-07 JP JP2012542507A patent/JP5779787B2/ja not_active Expired - Fee Related
- 2010-12-07 AU AU2010329998A patent/AU2010329998B2/en not_active Ceased
- 2010-12-08 UY UY33095A patent/UY33095A/es not_active Application Discontinuation
- 2010-12-09 AR ARP100104550A patent/AR079341A1/es unknown
- 2010-12-10 TW TW099143150A patent/TW201138799A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2010329998A1 (en) | 2012-07-05 |
| JP2013513567A (ja) | 2013-04-22 |
| AR079341A1 (es) | 2012-01-18 |
| EP2509967B1 (en) | 2016-02-17 |
| US20120302496A1 (en) | 2012-11-29 |
| JP5779787B2 (ja) | 2015-09-16 |
| EP2509967A1 (en) | 2012-10-17 |
| AU2010329998B2 (en) | 2015-05-21 |
| WO2011069995A1 (en) | 2011-06-16 |
| UY33095A (es) | 2011-07-29 |
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